Triethylamine → (3S,4S)-3-[2-(4-Methoxy-benzyl)-1-oxo-2,8-diaza-spiro[4.5]dec-8-ylmethyl]-4-phenyl-pyrrolidine-1-carboxylic Acid Tert-Butyl Ester

HRID 1182168Notes

Reaction equation

HRID 1182168 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:21]=[CH:20][C:7]([CH2:8][N:9]2[CH2:13][CH2:12][C:11]3([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[C:10]2=[O:19])=[CH:6][CH:5]=1.C(N(CC)CC)C.[C:29]([O:33][C:34]([N:36]1[CH2:40][C@H:39]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C@@H:38]([CH:47]=O)[CH2:37]1)=[O:35])([CH3:32])([CH3:31])[CH3:30].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[C:29]([O:33][C:34]([N:36]1[CH2:40][C@H:39]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C@@H:38]([CH2:47][N:16]2[CH2:15][CH2:14][C:11]3([C:10](=[O:19])[N:9]([CH2:8][C:7]4[CH:6]=[CH:5][C:4]([O:3][CH3:2])=[CH:21][CH:20]=4)[CH2:13][CH2:12]3)[CH2:18][CH2:17]2)[CH2:37]1)=[O:35])([CH3:32])([CH3:30])[CH3:31]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 450741222,8-Diazaspiro[4.5]decan-1-one, 2-[(4-methoxyphenyl)methyl]-, (Hydrochloride) (1:1)HCID 58981949(3R,4S)-3-formyl-4-phenyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 11284019(3S,4S)-3-[2-(4-Methoxy-benzyl)-1-oxo-2,8-diaza-spiro[4.5]dec-8-ylmethyl]-4-phenyl-pyrrolidine-1-carboxylic Acid Tert-Butyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 3.41 g of 2-(4-methoxy-benzyl)-2,8-diaza-spiro[4.5]decan-1-one hydrochloride (12.3 mmol) in dichloromethane (50 mL) was added triethylamine (1.71 mL, 12.3 mmol) followed by 3.85 g of (3R,4S)-3-formyl-4-phenyl-pyrrolidine-1-carboxylic acid tert-butyl ester (12.3 mmol) in dichloromethane (75 mL) and stirred for 1 h at room temperature. Sodium triacetoxyborohydride (3.91 g, 18.4 mmol) was then added and the reaction mixture stirred overnight at room temperature.

Workup

  1. stirringthe reaction mixture stirred overnight at room temperature

Sources & evidence

ORD record
ord-cc007023722e4e78b65d7da5bc0be681
Source dataset
uspto-grants-2007_10
Patent number
US07288548B2

Reaction notes

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