Sodium triacetoxyborohydride → 2-Diphenylmethyl-3-[(2-methoxy-5-(methylethyl)phenyl)methylamino]-4-(2-dimethylaminocarbamoyl-ethyl)pyrrolidine

HRID 1451493Notes

Reaction equation

HRID 1451493 reaction equation
[C:1]1([CH:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:8]2[CH:12]([NH2:13])[CH:11]([CH2:14][CH2:15][C:16](=[O:21])[NH:17][N:18]([CH3:20])[CH3:19])[CH2:10][NH:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:28][O:29][C:30]1[CH:37]=[CH:36][C:35]([CH:38]([CH3:40])[CH3:39])=[CH:34][C:31]=1[CH:32]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[C:22]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:8]2[CH:12]([NH:13][CH2:32][C:31]3[CH:34]=[C:35]([CH:38]([CH3:40])[CH3:39])[CH:36]=[CH:37][C:30]=3[O:29][CH3:28])[CH:11]([CH2:14][CH2:15][C:16](=[O:21])[NH:17][N:18]([CH3:20])[CH3:19])[CH2:10][NH:9]2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 70095025-ISOPROPYL-2-METHOXYBENZALDEHYDEHCID 67694043HCID 67694043, compound

Product 1

HCID 200880122-Diphenylmethyl-3-[(2-methoxy-5-(methylethyl)phenyl)methylamino]-4-(2-dimethylaminocarbamoyl-ethyl)pyrrolidineYield 62%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 100 mg (0.272 mmol) [(2SR, 3SR, 4RS)-2-diphenylmethyl-3-amino-4-(2-dimethylaminocarbamoylethyl)pyrrolidine](the product of Example 26B) in 25 ml of dichloroethane was treated with 48 mg (0.272 mmol) of 2-methoxy-5isopropylbenzaldehyde and 81 mg (0.381 mmol) of sodium triacetoxyborohydride. The reaction mixture was stirred for 18 hours and then quenched with 15 ml of saturated aqueous sodium bicarbonate. The reaction mixture was extracted with methylene chloride and the organic phase was washed with brine, dried and evaporated. The residue was chromatographed on silica gel eluting with 97/2/1 (methylene chloride/methanol/ammonia) to afford 89 mg (62%) of the title compound.

Workup

  1. customquenched with 15 ml of saturated aqueous sodium bicarbonate
  2. extractionThe reaction mixture was extracted with methylene chloride
  3. washthe organic phase was washed with brine
  4. customdried
  5. customevaporated
  6. customThe residue was chromatographed on silica gel eluting with 97/2/1 (methylene chloride/methanol/ammonia)

Sources & evidence

ORD record
ord-c7681c6b7cd9480e82a475df99bd3bb4
Source dataset
uspto-grants-1997_02
Patent number
US05604252

Reaction notes

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