Sodium borohydride → HCID 68455343, compound

HRID 2357625Notes

Reaction equation

HRID 2357625 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) before sodium borohydride (268 mg, 7078 μmol) and tetrakis(triphenylphosphine)palladium(0) (102 mg, 88 μmol) were added at ambient. 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). MS (ES+): 171(M+H)+.

Workup

  1. additionwere added at ambient
  2. filtrationthen filtered through a pad of silica gel
  3. washwashed with chloroform
  4. customto remove impurities
  5. washThe silica was washed again with methanol

Sources & evidence

ORD record
ord-886493d56fc444ea9026b0e69b50dec6
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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