Sodium cyanoborohydride → HCID 70440931, compound

HRID 745466Notes

Reaction equation

HRID 745466 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[C@@H:10]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:11]=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[CH2:39]([NH3+:43])[CH:40]([CH3:42])[CH3:41].C([BH3-])#N.[Na+]>CO>[CH2:39]([NH:43][CH2:11][C@@H:10]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[CH:40]([CH3:42])[CH3:41]

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydride2×HCID 18631395HCID 18631395, compoundHCID 20200746HCID 20200746, compound

Product 1

HCID 70440931HCID 70440931, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (S)-3-t-butoxycarbonylamino-(R)-2-benzyloxy-4-cyclohexylbutyraldehyde (600 mg.) and isobutylammonium p-toluenesulfonate (510 mg.) were stirred together in methanol for 30 minutes at 20° C. and then treated in one portion with sodium cyanoborohydride (105 mg.). After 45 minutes 28 mg. more sodium cyanoborohydride was added and 30 minutes later the mixture was filtered through Celite, concentrated, the residue dissolved in ethyl acetate which was washed twice with aqueous bicarbonate, brine and dried over sodium sulfate. After solvent removal 600 mg. (87%) of the title amine was obtained which was used without additional purification.

Workup

  1. filtrationwas filtered through Celite
  2. concentrationconcentrated
  3. dissolutionthe residue dissolved in ethyl acetate which
  4. washwas washed twice with aqueous bicarbonate, brine
  5. dry with materialdried over sodium sulfate
  6. customAfter solvent removal 600 mg

Sources & evidence

ORD record
ord-68aca937420d448683cd58247084a07c
Source dataset
uspto-grants-1986_07
Patent number
US04599198

Reaction notes

Loading…