Lithium borohydride → HCID 22730044, compound

HRID 2085792Notes

Reaction equation

HRID 2085792 reaction equation
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C@H:12]([C:21](OC)=[O:22])[CH2:13][S:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:7]([N+:25]([O-:27])=[O:26])[CH:6]=1)(=[O:4])=[O:3].[BH4-].[Li+]>C1COCC1.CO.C(OCC)(=O)C>[OH:22][CH2:21][CH:12]([NH:11][C:8]1[CH:9]=[CH:10][C:5]([S:2]([NH2:1])(=[O:3])=[O:4])=[CH:6][C:7]=1[N+:25]([O-:27])=[O:26])[CH2:13][S:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 2

HCID 4148881Lithium borohydrideHCID 68453896HCID 68453896, compound

Product 1

HCID 22730044HCID 22730044, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Example 434A (1.42 g, 3.45 mmol) in THF (10 mL) and methanol (1 mL) at room temperature was slowly treated with lithium borohydride (100 mg), stirred for 3 hours, as diluted with ethyl acetate (100 mL), washed with water (45 mL) and brine (10 mL), dried (MgSO4), filtered, and concentrated to provide the desired product. MS (ESI(+)) m/e 384 (M+H).

Workup

  1. washwashed with water (45 mL) and brine (10 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3a82b7a25b7a43129b963361600a6773
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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