Sodium triacetoxyborohydride → HCID 86757027, compound

HRID 1068194Notes

Reaction equation

HRID 1068194 reaction equation
[C:1]1([C:7]2[S:8][C:9]([CH:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)=[CH:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:18]([C@@H:20]1[C@@H:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:23][N:22]([C@H:31]([CH:44]2[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]2)[C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=2)=[O:33])[CH2:21]1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:1]1([C:7]2[S:8][C:9]([CH:12]3[CH2:17][CH2:16][N:15]([CH2:18][C@@H:20]4[C@@H:24]([C:25]5[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=5)[CH2:23][N:22]([C@H:31]([CH:44]5[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]5)[C:32]([O:34][CH2:35][C:36]5[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=5)=[O:33])[CH2:21]4)[CH2:14][CH2:13]3)=[CH:10][N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 21193060HCID 21193060, compoundHCID 53654320alpha-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid 4-methoxybenzyl ester

Product 1

HCID 86757027HCID 86757027, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To 12 mg of 4-(2-phenyl-thiazol-5-yl)-piperidine (from Step B) in 3 ml of DCE was added 35 mg of a-(R)-(3-(R)-formyl4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid, p-methoxybenzyl ester (prepared above as Aldehyde 5) followed by 19 mg of sodium triacetoxyborohydride. The reaction was stirred overnight at room temperature. The solvent was evaporated under reduced pressure. The residue was purified by flash chromatography with 10% EtOAc in hexane followed by 50% EtOAc in hexane to give 28 mg of the title compound.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customThe residue was purified by flash chromatography with 10% EtOAc in hexane

Sources & evidence

ORD record
ord-665e81dda74a4763b52d56872a2c06a5
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

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