Water → 1-tert-Butoxycarbonylamino-6-hydroxyheptane

HRID 1007289Notes

Reaction equation

HRID 1007289 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:16][Mg]Br.O>O1CCCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([OH:15])[CH3:16])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 10536636tert-Butyl 6-oxohexylcarbamateHCID 178418573HCID 178418573, compound

Product 1

HCID 226679381-tert-Butoxycarbonylamino-6-hydroxyheptane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under argon atmosphere, a solution of 650 mg of 6-tert-butoxycarbonylaminohexanal in 10 mL of anhydrous tetrahydrofuran was cooled to −78° C., and treated dropwise with 6.8 mL of methylmagnesium bromide (a 1.0 M solution in tetrahydrofuran). After 2 hours, the reaction solution was combined with water, extracted with ethyl acetate, and dried. After concentrating, the residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:1) to obtain 280 mg of the desirable compound.

Workup

  1. extractionextracted with ethyl acetate
  2. customdried
  3. concentrationAfter concentrating
  4. customthe residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-6e87fa16ce964a8aa3e634e6ef30806e
Source dataset
uspto-grants-2004_09
Patent number
US06794389B2

Reaction notes

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