6-Bromo-1-hexanol → 6-(Tert-butyloxycarbonylaminooxy)hexan-1-ol

HRID 24956

Reaction equation

HRID 24956 reaction equation
C1CCN2C(=NCCC2)CC1.[C:12]([O:16][C:17]([NH:19][OH:20])=[O:18])([CH3:15])([CH3:14])[CH3:13].Br[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][OH:28]>C(Cl)Cl>[C:12]([O:16][C:17]([NH:19][O:20][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][OH:28])=[O:18])([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 779706-Bromo-1-hexanolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 97534tert-butyl N-hydroxycarbamate

Product 1

HCID 117911126-(Tert-butyloxycarbonylaminooxy)hexan-1-olYield 77.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 179 μL (183 mg, 1.2 mmol) of DBU in 1 mL of CH2Cl2 was added 133 mg (1.0 mmol) of N-(tert-butyloxycarbonyl)hydroxylamine (Aldrich Chemical Co.) and 157 μL (217 mg, 1.2 mmol) of 6-bromohexan-1-ol (Aldrich Chemical Co.), and the mixture was stirred for 18 hours at room temperature. The mixture was concentrated to give a yellow oil. Purification by silica gel chromatography (35/5/65 EtOAc/MeOH/hexanes) gave 180 mg (77%) of compound 27 as a colorless oil: 1H NMR (CDCl3) δ 1.39 (m, 4H), 1.48 (s, 9H), 1.59 (m, 4H), 3.63 (t, 2H), 3.85 (t, 2H), 7.42 (s, 1H); 13C NMR (CDCl3) δ 25.6, 25.8, 28.1, 28.4, 62.8, 76.8, 81.7, 157.2.

Workup

  1. concentrationThe mixture was concentrated
  2. customto give a yellow oil
  3. customPurification by silica gel chromatography (35/5/65 EtOAc/MeOH/hexanes)

Sources & evidence

ORD record
ord-0ed7e9177c5342ad974e72409fd7ae88
Source dataset
uspto-grants-2005_02
Patent number
US06858210B1

Linked notes

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