Sodium cyanoborohydride → HCID 59655579, compound

HRID 2053463Notes

Reaction equation

HRID 2053463 reaction equation
C([O:3][C:4](=O)[C@@:5]([NH2:24])([CH2:22][CH3:23])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:10][CH:9]=1)C.[BH3-][C:27]#N.[Na+]>ClCCl.C(O)=O>[CH2:22]([C@@:5]([NH:24][CH3:27])([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:10][CH:9]=1)[CH2:4][OH:3])[CH3:23]

Participants

5

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 69203904HCID 69203904, compound

Product 1

HCID 59655579HCID 59655579, compound

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

(R)-2-amino-2-ethyl-4-(4-heptyloxy-phenyl)-butyric acid ethyl ester (175 mg; 0.5 mmol) is dissolved in dichloromethane (2) and formic acid (100 μl), p-formaldehyde (100 μl; 30% in water) and NaBH3CN are added. After 1 hour at RT the reaction mixture is extracted with saturated aqueous NaHCO3 solution and the organic layer is dried over MgSO4 and purified on silica gel using n-hexanetethyl acetate (1/1→1/9) as mobile phase.

Workup

  1. extractionAfter 1 hour at RT the reaction mixture is extracted with saturated aqueous NaHCO3 solution
  2. dry with materialthe organic layer is dried over MgSO4
  3. custompurified on silica gel using n-hexanetethyl acetate (1/1→1/9) as mobile phase

Sources & evidence

ORD record
ord-ca0b0151900d4995b67e9464dafa660a
Source dataset
uspto-grants-2008_02
Patent number
US07326801B2

Reaction notes

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