Sodium cyanoborohydride → HCID 68648374, compound

HRID 1161775Notes

Reaction equation

HRID 1161775 reaction equation
N1C2=CC=C(N)CC2NC1.C([BH3-])#N.[Na+].[CH2:15]([O:22][C:23]1[CH:44]=[C:43]([Cl:45])[C:26]([CH2:27][CH:28]2[CH2:32][CH2:31][N:30]([N:33]3[C:37]4[CH2:38][CH2:39][CH2:40][CH2:41][C:36]=4[N:35]=[CH:34]3)[C:29]2=[O:42])=[C:25]([Cl:46])[CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CO.C(OCC)(=O)C>[CH2:15]([O:22][C:23]1[CH:44]=[C:43]([Cl:45])[C:26]([CH2:27][C@@H:28]2[CH2:32][CH2:31][N:30]([N:33]3[C:37]4[CH2:38][CH2:39][CH2:40][CH2:41][C:36]=4[N:35]=[CH:34]3)[C:29]2=[O:42])=[C:25]([Cl:46])[CH:24]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 68648055HCID 68648055, compoundHCID 68648217HCID 68648217, compound

Product 1

HCID 68648374HCID 68648374, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add Preparation 10 (5.25 g) to a suspension of imidazolocyclohexy-3-amine hydrochloride (2 gm) (Preparation 8) in methanol (30 mL). Stir the mixture at room temperature for 30 min. Add sodium cyanoborohydride (1 g) and stir the mixture for 2 h. Heat the reaction mixture at 50° C. for 2 h. Dilute the reaction mixture with ethyl acetate (50 mL) and wash the mixture with water (50 mL). Dry ethyl acetate layer over sodium sulfate and concentrate on rotary evaporator to give a crude. Purify the crude by silica flash chromatography eluting with a gradient of 0-5% methanol in DCM to give the product as a mixture of diastereomers, 3-(4-benzyloxy-2,6-dichloro-benzyl)-1-(4,5,6,7-tetrahydro-3H-benzimidazole-3-yl)-pyrrolidin-2-one (4.5 gm). MS: m/z=470 (M+1).

Workup

  1. additionAdd
  2. temperatureHeat the reaction mixture at 50° C. for 2 h
  3. washwash the mixture with water (50 mL)
  4. concentrationDry ethyl acetate layer over sodium sulfate and concentrate on rotary evaporator
  5. customto give a crude
  6. customPurify the crude by silica flash chromatography
  7. washeluting with a gradient of 0-5% methanol in DCM
  8. customto give the product

Sources & evidence

ORD record
ord-b489c842f7d94d9fbe6a491006714aac
Source dataset
uspto-grants-2010_10
Patent number
US07820659B2

Reaction notes

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