Water → HCID 86674063, compound

HRID 2404966Notes

Reaction equation

HRID 2404966 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][C@H:8]([CH3:18])[C:9]([N:11]1[O:16][CH:15]2[CH2:17][CH:12]1[CH:13]=[CH:14]2)=[O:10])([CH3:4])([CH3:3])[CH3:2].C[N+]1([O-])CC[O:24]CC1.[OH2:28]>[Os](=O)(=O)(=O)=O>[OH:28][CH:14]1[CH:13]([OH:24])[CH:12]2[CH2:17][CH:15]1[O:16][N:11]2[C:9](=[O:10])[C@H:8]([NH:7][C:6](=[O:19])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 86674062HCID 86674062, compound

Product 1

HCID 86674063HCID 86674063, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

A solution of tert-butyl-(R)-1-(3-oxa-2-aza-bicyclo[2.2.1]hept-5-en-2-yl)-1-oxopropan-2-ylcarbamate (27.3 g, 101.75 mmol, 1.00 equiv.) in teterahydrofuran:water (5:1) (600 mL), osmium tetroxide (230 mg, 0.90 mmol, 0.01 equiv.), and N-methylmorpholine-N-oxide (25.26 g, 215.62 mmol, 2.10 equiv.) was stirred at about 20° C. for about 50 minutes. After adding sodium thiolsulfate (22 g), the resulting solution was extracted with ethyl acetate (3×200 mL) and the organic layers combined. The organic phase was washed with a saturated sodium bicarbonate solution (1×250 mL) and then concentrated in vacuo to give the desired product as a yellow liquid (30.1 g; yield=98%). 1H NMR (300 MHz, CDCl3) δ: 5.29 (b, 1H), 4.36-4.74 (m, 3H), 3.76-4.09 (m, 4H), 2.67 (m, 1H), 1.90 (m, 1H), 1.43 (s, 9H), 1.30 (d, J=6.9 Hz, 3H).

Workup

  1. extractionthe resulting solution was extracted with ethyl acetate (3×200 mL)
  2. washThe organic phase was washed with a saturated sodium bicarbonate solution (1×250 mL)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2f941a86d9ed488c8c0ddbe90608373d
Source dataset
uspto-grants-2014_08
Patent number
US08802850B2

Reaction notes

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