2-Bromoethanol → Tert-butyl[3-(2-hydroxyethyl)-3-azabicyclo[3.1.0]hex-6-yl]carbamate

HRID 255256Notes

Reaction equation

HRID 255256 reaction equation
[CH:1]12[CH:6]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH:5]1[CH2:4][NH:3][CH2:2]2.Br[CH2:16][CH2:17][OH:18].C(Cl)(Cl)Cl.CO>C(#N)C>[OH:18][CH2:17][CH2:16][N:3]1[CH2:2][CH:1]2[CH:5]([CH:6]2[NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:4]1

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 111483086-(BOC-amino)-3-azabicyclo[3.1.0]hexaneHCID 21584188Chloroform methanol

Product 1

HCID 86642627Tert-butyl[3-(2-hydroxyethyl)-3-azabicyclo[3.1.0]hex-6-yl]carbamateYield 46%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of tert-butyl 3-azabicyclo[3.1.0]hex-6-ylcarbamate (T. F. Braish et al. Synlett, 1996, page 1100 and T. Norris et al. J. Chem. Soc. Perkin I, 2000, page 1615-1622), 2-bromoethanol (669 mg, 3.36 mmol) and N,N-ethyldiisopropyl amine (0.087 mL) in acetonitrile (9 mL) was heated in the microwave at 70° C. for 30 minutes. Chromatography on silica gel with chloroform/methanol (20:1) gave 376 mg (46%) of the product.

Sources & evidence

ORD record
ord-f99ec9f49404451e9086b8b5f016a2a0
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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