Water → HCID 22711812, compound

HRID 349204Notes

Reaction equation

HRID 349204 reaction equation
[BH4-].[Na+].[O:3]=[C:4]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[NH:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1.O>O1CCCC1.CO>[OH:3][CH:4]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[NH:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[CH2:18][CH2:17]1

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 68823456HCID 68823456, compound

Product 1

HCID 22711812HCID 22711812, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

NaBH4 (0.034 mol) was added portionwise at 5° C. to a mixture of (±)-1,1-dimethyl-ethyl 4-[[1-(2-oxo-2-phenylethyl)-1H-benzimidazol-2-yl]amino]-1-piperidinecarboxylate (0.034 mol) in tetrahydrofuran (250 ml) and methanol (250 ml). The mixture was stirred at 5° C. and then hydrolyzed cold with H2O. The solvent was evaporated and the residue was taken up in H2O. The precipitate was filtered off, washed with diisopropyl-ether and dried, yielding 11.3 g of (±)-1,1-dimethylethyl 4-[[1-(2-hydroxy-2-phenyl-ethyl)-1H-benzimidazol-2-yl]amino]-1-piperidinecarboxylate (76%) (interm. 3).

Workup

  1. customThe solvent was evaporated
  2. filtrationThe precipitate was filtered off
  3. washwashed with diisopropyl-ether
  4. customdried

Sources & evidence

ORD record
ord-a405183bc443440e94ec92bf62f7bfae
Source dataset
uspto-grants-2007_02
Patent number
US07179811B2

Reaction notes

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