Formaldehyde → 10-Chloro-1,2-dimethyl-8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole

HRID 2423203Notes

Reaction equation

HRID 2423203 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=O.[Cl:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]3OC[CH2:20][NH:19][CH:18]([CH3:23])[C:16]3=2)[N:11]([S:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)(=[O:26])=[O:25])[CH:10]=1.C=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO.C1COCC1>[Cl:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]3[O:5][CH2:3][CH2:2][N:19]([CH3:20])[CH:18]([CH3:23])[C:16]3=2)[N:11]([S:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)(=[O:26])=[O:25])[CH:10]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 6724199710-Chloro-1-methyl-8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole trifluoroacetate

Product 1

HCID 2505500810-Chloro-1,2-dimethyl-8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indoleYield 49.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

10-Chloro-1-methyl-8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole trifluoroacetate (Example 98, 59 mg, 0.15 mmol) in MeOH (1 mL) was converted to the free amine by PL-HCO3 MP SPE (Polymer Laboratories) column. Formaldehyde (37 wt. % in H2O, 0.20 mL, 2.4 mmol) was added to a solution of the free amine (0.15 mmol) in THF (1 mL). After stirring for 10 minutes at room temperature sodium triacetoxyborohydride (26 mg, 0.12 mmol) was added and the mixture was stirred for an additional 30 minutes and evaporated. The crude material was purified by preparative HPLC (Xterra C18, 10 mM NH4HCO3 (pH 10) —CH3CN) to give the title compound as a white solid (28.9 mg). MS m/z 391 [M+H]+.

Workup

  1. additionwas added
  2. customevaporated
  3. customThe crude material was purified by preparative HPLC (Xterra C18, 10 mM NH4HCO3 (pH 10) —CH3CN)

Sources & evidence

ORD record
ord-132e0c4fa4b24302b3c726cea34b6369
Source dataset
uspto-grants-2011_06
Patent number
US07960374B2

Reaction notes

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