Acetic Acid → HCID 69546069, compound

HRID 1796986Notes

Reaction equation

HRID 1796986 reaction equation
C(O[C@H:5]1[CH2:9][C@@H:8]([N:10]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:7]=[CH:6]1)(=O)C.[BH4-].[Na+].C(O)(=O)C>C(O)(C)C.O1CCCC1.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>[CH3:16][C:14]([CH3:17])([O:13][C:11]([N:10]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@@H:8]1[CH2:9][CH2:5][CH:6]=[CH:7]1)=[O:12])[CH3:15]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 69546006HCID 69546006, compound

Product 1

HCID 69546069HCID 69546069, compoundYield 79.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1S-cis)-4-(di-tert-butoxycarbonylamino)cyclopent-2-enyl acetate (prepared as described by D. Zhang et.al. Tett. Lett. 1996, 3799–3802) (8.98 g), tetrakis(triphenylphosphine)palladium(0) (0.463 g) in isopropanol (135 ml) and tetrahydrofuran (135 ml) was added sodium borohydride (4.97 g) portionwise at 0° C. The mixture was stirred at 0° C. for 3 hours before the careful dropwise addition of glacial acetic acid (20 ml). The solution was concentrated in vacuo and the residue purified by chromatography (SiO2, diethylether 1:9 isohexane as eluent) to afford the sub-title compound (5.90 g).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customthe residue purified by chromatography (SiO2, diethylether 1:9 isohexane as eluent)

Sources & evidence

ORD record
ord-ab3493598196468d8d2a5ed5a3d6aedb
Source dataset
uspto-grants-2006_04
Patent number
US07034032B2

Reaction notes

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