Lithium borohydride → HCID 69039557, compound

HRID 1242817Notes

Reaction equation

HRID 1242817 reaction equation
[C:1]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:6]=[CH:5][C:4]([C:7]([N:9]2[CH2:17][C@H:16]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH2:15][C@H:10]2[C:11](OC)=[O:12])=[O:8])=[CH:3][CH:2]=1.[BH4-].[Li+]>C1COCC1>[C:1]1([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:2]=[CH:3][C:4]([C:7]([N:9]2[CH2:17][C@H:16]([O:18][Si:19]([C:22]([CH3:23])([CH3:25])[CH3:24])([CH3:21])[CH3:20])[CH2:15][C@H:10]2[CH2:11][OH:12])=[O:8])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 86602441HCID 86602441, compound2×

Product 1

HCID 69039557HCID 69039557, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl (4R)-1-(1,1′-biphenyl-4-ylcarbonyl)-4-{[tert-butyl (dimethyl) silyl]oxy}-L-prolinate (intermediate 15a, 2.61 g, 5.94 mmol) in THF (60 ml) was cooled to 0° C. and treated with lithium borohydride (95%, 206 mg, 8.9 mmol). The reaction mixture was stirred for 3 h and quenched slowly with water. THF was removed under reduced pressure, the crude was redissolved in AcOEt, washed with sat. NH4Cl, brine, dried over magnesium sulfate, filtered and concentrated.

Workup

  1. customquenched slowly with water
  2. customTHF was removed under reduced pressure
  3. dissolutionthe crude was redissolved in AcOEt
  4. washwashed with sat. NH4Cl, brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a4d9ae3428134f798bc245a86484c39b
Source dataset
uspto-grants-2006_10
Patent number
US07115754B2

Reaction notes

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