Sodium Azide → Phenylmethyl 3-azido-4-hydroxy-1-pyrrolidinecarboxylate

HRID 1398023Notes

Reaction equation

[CH:1]12[O:6][CH:5]1[CH2:4][N:3]([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[CH2:2]2.[N-:17]=[N+:18]=[N-:19].[Na+]>CN(C=O)C.CC(C)=O.O.CCOCC>[N:17]([CH:1]1[CH:5]([OH:6])[CH2:4][N:3]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:2]1)=[N+:18]=[N-:19]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred mixture of benzyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate (5.2 g, 23.72 mmol) (Method 197) in DMF (30 mL) was added sodium azide (2.313 g, 35.58 mmol) in a mixture of acetone (20.00 mL) and water (10.00 mL). The resulting mixture was stirred at 80° C. for 24 h. The mixture was then diluted with water and ether, separated, and the organic layer was washed with brine, dried and conc. in vacuo. The resulting material was purified via silica gel chromatography (eluted with 15% to 35% ethyl acetate/hexane), yielding the title compound as a yellow solid (4.10 g, 65.9%). 1H NMR (400 MHz, dichloromethane-d2) δ ppm 7.50-7.25 (m, 5 H), 5.43-5.25 (m, 2 H), 4.31 (brs, 1 H), 4.00 (brs, 1 H), 3.77 (dd, 1 H), 3.69 (dd, 1 H), 3.53 (d, 1 H), 3.44 (dd, 1 H), 2.17 (brs, 1 H); m/z 263.

Workup

customseparated
washthe organic layer was washed with brine
customdried and conc. in vacuo
customThe resulting material was purified via silica gel chromatography (eluted with 15% to 35% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-a3e5487e861d4499b52363294d44328a
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901307B2

Reaction notes

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