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2-[2-(Benzyloxy)ethoxy]ethan-1-ol → methyl (7R)-7-({2-[2-(benzyloxy)ethoxy]ethyl}amino)-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

HRID 1669462
Notes
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Reaction equation

HRID 1669462 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:15][C@@H:16]1[CH2:23][N:22]2[C:24]3[CH:25]=[C:26]([C:37]([O:39][CH3:40])=[O:38])[CH:27]=[CH:28][C:29]=3[C:30]([CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)=[C:21]2[C:20]2[CH:41]=[CH:42][CH:43]=[CH:44][C:19]=2[O:18][CH2:17]1.[BH3-]C#N.[Na+]>C(OC)(OC)OC>[CH2:1]([O:8][CH2:9][CH2:10][O:11][CH2:12][CH:13]=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:1]([O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][NH:15][C@@H:16]1[CH2:23][N:22]2[C:24]3[CH:25]=[C:26]([C:37]([O:39][CH3:40])=[O:38])[CH:27]=[CH:28][C:29]=3[C:30]([CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)=[C:21]2[C:20]2[CH:41]=[CH:42][CH:43]=[CH:44][C:19]=2[O:18][CH2:17]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 2297222-[2-(Benzyloxy)ethoxy]ethan-1-olHCID 5003444Sodium cyanoborohydrideHCID 50994751Methyl(7r)-7-amino-14-cyclohexyl-7,8-dihydro-6h-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

Product 2

HCID 58885153(2-Benzyloxy-ethoxy)-acetaldehydeHCID 67346704
methyl (7R)-7-({2-[2-(benzyloxy)ethoxy]ethyl}amino)-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate
Yield 35%

Reagents, catalysts & solvents 1

HCID 9005Trimethyl orthoformateSolvent

Procedure

[2-(benzyloxy)ethoxy]acetaldehyde was prepared by Swern oxidation of commercially available 2-[2-(benzyloxy)ethoxy]ethanol. A 0.15M solution of the foregoing aldehyde and methyl (7R)-7-amino-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (prepared as described in Example 1, Step 4) in CH(OMe)3 was stirred overnight at RT; the residue obtained after removing volatiles in vacuo was dissolved in MeOH (0.15M solution), NaCNBH3 (2.3 eq) was added and the mixture was left stirring for 4 h. All volatiles were evaporated and the residual material was dissolved in EtOAc and washed with sat. aq. NaHCO3 and brine. After drying over Na2SO4 all volatiles were evaporated in vacuo; FC (Biotage, PE/EtOAc 1:1 to 1:3 with 0.5% NEt3) afforded 35% of methyl (7R)-7-({2-[2-(benzyloxy)ethoxy]ethyl}amino)-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate.

Workup

  1. customthe residue obtained
  2. customafter removing volatiles in vacuo
  3. dissolutionwas dissolved in MeOH (0.15M solution)
  4. waitthe mixture was left
  5. customAll volatiles were evaporated
  6. dissolutionthe residual material was dissolved in EtOAc
  7. washwashed with sat. aq. NaHCO3 and brine
  8. dry with materialAfter drying over Na2SO4 all volatiles
  9. customwere evaporated in vacuo

Sources & evidence

ORD record
ord-11233c1de676465c9585314ca17af160
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07989438B2

Reaction notes

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