Lithium tri-s-butylborohydride → HCID 66662305, compound

HRID 2275664Notes

Reaction equation

HRID 2275664 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]2[C:9]3([O:26][C:27](=[O:28])[C:5]=2[CH:4]=1)[CH2:13][CH2:12][N:11]([C:14]([C:16]1([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)[CH2:18][CH2:17]1)=[O:15])[CH2:10]3.CCC(C)[BH-](C(C)CC)C(C)CC.[Li+]>O1CCCC1.O>[OH:2][C:3]1[CH:8]=[CH:7][C:6]2[C:9]3([O:26][C:27](=[O:28])[C:5]=2[CH:4]=1)[CH2:13][CH2:12][N:11]([C:14]([C:16]1([C:19]2[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=2)[CH2:17][CH2:18]1)=[O:15])[CH2:10]3

Participants

5

Reactant 2

HCID 3611392Lithium tri-s-butylborohydrideHCID 66661979HCID 66661979, compound

Product 1

HCID 66662305HCID 66662305, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-methoxy-1′-{[1-(4-methylphenyl)cyclopropyl]carbonyl}-3H-spiro[2-benzofuran-1,3′-pyrrolidin]-3-one (40 mg, 0.0001 mol) in tetrahydrofuran (2 mL, 0.02 mol) was added. L-Selectride® in tetrahydrofuran (1.0 M, 0.53 mL) and the resulting solution was heated to 120° C. for 50 minutes using microwave irradiation. To the reaction mixture was added a few drops of water to quench the reaction. Then the reaction mixture was concentrated and about. 3 mL of concentrated HCl aqueous solution was added to dissolve the residue. The resulting solution was stirred at rt for 2 h. The crude product was purified using prep-HPLC. LCMS: m/z 364.2 (M+H)+.

Workup

  1. custommicrowave irradiation
  2. customto quench
  3. customthe reaction
  4. concentrationThen the reaction mixture was concentrated
  5. addition3 mL of concentrated HCl aqueous solution was added
  6. dissolutionto dissolve the residue
  7. customThe crude product was purified

Sources & evidence

ORD record
ord-4f60e2c800424d4a8fdc91182f25da30
Source dataset
uspto-grants-2015_09
Patent number
US09126927B2

Reaction notes

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