6-Amino-1-hexanol → tert-Butyl N-(6-hydroxyhexyl)carbamate

HRID 1464542Notes

Reaction equation

HRID 1464542 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].[C:9]([O:13][C:14](ON=C(C1C=CC=CC=1)C#N)=[O:15])([CH3:12])([CH3:11])[CH3:10]>C(Cl)(Cl)Cl>[C:9]([O:13][C:14]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8])=[O:15])([CH3:12])([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 199606-Amino-1-hexanolHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

Product 1

HCID 4146612tert-Butyl N-(6-hydroxyhexyl)carbamateYield 106.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Four grams of 6-amino-1-hexanol (34.1 mmols) was dissolved in 30 ml of chloroform and ice-cooled. Seven grams of 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile (BOC-ON) dissolved in 20 ml of chloroform was added, and the mixture was ice-cooled and reacted for 16 hours. Chloroform was evaporated, and the residue was separated and purified by silica gel column chromatography to obtain 6.59 g of the captioned compound. Yield: 89 %.

Workup

  1. temperatureice-cooled
  2. additionwas added
  3. temperaturecooled
  4. customreacted for 16 hours
  5. customChloroform was evaporated
  6. customthe residue was separated
  7. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-95876869716c4791800e581622c6539b
Source dataset
uspto-grants-1994_04
Patent number
US05306617

Reaction notes

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