Sodium borohydride → HCID 68455343, compound

HRID 2357609Notes

Reaction equation

HRID 2357609 reaction equation
[CH:1]([NH:4][C:5]([C@H:7]1[CH2:11][CH2:10][CH:9]([CH3:12])[N:8]1C(OCC=C)=O)=[O:6])([CH3:3])[CH3:2].[BH4-].[Na+]>C(#N)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:1]([NH:4][C:5]([C@H:7]1[CH2:11][CH2:10][CH:9]([CH3:12])[NH:8]1)=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 86607614HCID 86607614, compound

Product 1

HCID 68455343HCID 68455343, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

(R)-Allyl 2-(isopropylcarbamoyl)-5-methylpyrrolidine-1-carboxylate (450 mg, 1769 μmol) was dissolved in acetonitrile (13 mL) and sodium borohydride (268 mg, 7078 μmol) and tetrakis(triphenylphosphine)palladium(0)(102 mg, 88 μmol) were added at ambient temperature. The reaction mixture was heated to 50° C. for 4 h, then filtered through a pad of silica gel and washed with chloroform to remove impurities. The silica was washed again with methanol to obtain the title compound as a mixture of diastereomers (˜60:40). Found MS (ES+): 171(M+H)+.

Workup

  1. filtrationfiltered through a pad of silica gel
  2. washwashed with chloroform
  3. customto remove impurities
  4. washThe silica was washed again with methanol

Sources & evidence

ORD record
ord-7085ea27014f4d6abd0979f4159a7a4e
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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