Lithium tri-s-butylborohydride → HCID 66662305, compound

HRID 557953Notes

Reaction equation

HRID 557953 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×

Conditions

Temperature
120 °C

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-3eabdd1519d844d7b06ae3a92e462710
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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