Sodium Hydroxide → HCID 15454896, compound

HRID 2287521Notes

Reaction equation

HRID 2287521 reaction equation
[NH2:1][C@H:2]1[C@H:6]([C:7]([O:9][CH3:10])=[O:8])[C@@H:5]([CH3:11])[N:4]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[C@H:3]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[CH3:28][O:29][C:30]1[CH:37]=[CH:36][C:35]([O:38][C:39]([F:42])([F:41])[F:40])=[CH:34][C:31]=1[CH:32]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>C(Cl)Cl>[CH2:15]([O:14][C:12]([N:4]1[C@H:5]([CH3:11])[C@H:6]([C:7]([O:9][CH3:10])=[O:8])[C@H:2]([NH:1][CH2:32][C:31]2[CH:34]=[C:35]([O:38][C:39]([F:40])([F:41])[F:42])[CH:36]=[CH:37][C:30]=2[O:29][CH3:28])[C@@H:3]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:13])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 27833642-Methoxy-5-(trifluoromethoxy)benzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 70302450HCID 70302450, compound

Product 1

HCID 15454896HCID 15454896, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (2S*,3S*,4S*,5R*)-3-amino-1-benzyloxycarbonyl-4-methoxycarbonyl-5-methyl-2-phenylpyrrolidine (793 mg, 2.15 mmol) and 2-methoxy-5-trifluoromethoxybenzaldehyde (569 mg, 2.58 mmol) in dry CH2Cl2 (10 ml) was added NaBH(OAc)3 (639 mg, 3.01 mmol) portionwise at room temperature. After stirring for 2 h at room temperature, the reaction mixture was basified to pH 10-11 by adding 10% NaOH aq. solution with ice-cooling. The organic layer was separated, and the aqueous layer was extracted with CH2Cl2 (60 ml×4). The combined CH2Cl2 solution was washed with brine, dried (MgSO4) and concentrated in vacuo to give crude title compound (1.32 g) as a yellow viscous oil. This was purified by column chromatography on silica gel (65 g) with hexane-ethyl acetate (3:1-2:1) to give the pure title compound (1.08 g, 88%) as a pale yellow oil.

Workup

  1. temperaturecooling
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with CH2Cl2 (60 ml×4)
  4. washThe combined CH2Cl2 solution was washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto give crude title compound (1.32 g) as a yellow viscous oil
  8. customThis was purified by column chromatography on silica gel (65 g) with hexane-ethyl acetate (3:1-2:1)

Sources & evidence

ORD record
ord-294df0769dcf4387bfeccaaf01c324f6
Source dataset
uspto-grants-2000_07
Patent number
US06083943

Reaction notes

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