Sodium triacetoxyborohydride → 2-Diphenylmethyl-3-[(2-methoxy-5-(1-methylethyl)phenyl)methylamino]-4-(2-methoxyethyl)pyrrolidine

HRID 1451494Notes

Reaction equation

HRID 1451494 reaction equation
[C:1]1([CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:8]2[CH:12]([NH2:13])[CH:11]([CH2:14][CH2:15][O:16][CH3:17])[CH2:10][NH:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:24][O:25][C:26]1[CH:33]=[CH:32][C:31]([CH:34]([CH3:36])[CH3:35])=[CH:30][C:27]=1[CH:28]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[C:18]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:8]2[CH:12]([NH:13][CH2:28][C:27]3[CH:30]=[C:31]([CH:34]([CH3:36])[CH3:35])[CH:32]=[CH:33][C:26]=3[O:25][CH3:24])[CH:11]([CH2:14][CH2:15][O:16][CH3:17])[CH2:10][NH:9]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 70095025-ISOPROPYL-2-METHOXYBENZALDEHYDEHCID 676941482-Diphenylmethyl-3-amino-4-(2-methoxyethyl)pyrrolidine

Product 1

HCID 676940972-Diphenylmethyl-3-[(2-methoxy-5-(1-methylethyl)phenyl)methylamino]-4-(2-methoxyethyl)pyrrolidineYield 62%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 109 mg (0.35 mmol) of [(2SR, 3SR, 4RS)-2-diphenylmethyl-3-amino-4-(2-methoxyethyl)pyrrolidine] (the product of Example 27B) in 35 ml of dichloroethane was treated with 63 mg (0.35 mmol) of 2-methoxy-5-isopropylbenzaldehyde and 104 mg (0.49 mmol) of sodium triacetoxyborohydride. The reaction mixture was stirred for 18 hours and then quenched with 30 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 102 mg (62%) of the title compound.

Workup

  1. customquenched with 30 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-7ed3a4bdb4254622a9d5cdf0a6414844
Source dataset
uspto-grants-1997_02
Patent number
US05604252

Reaction notes

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