Methyl morpholine oxide → HCID 131734578, compound

HRID 595255Notes

Reaction equation

HRID 595255 reaction equation
C[N+]1([O-])CC[O:5]CC1.[C:9]([O:13][C:14](=[O:21])[NH:15][C:16]1([CH:19]=[CH2:20])[CH2:18][CH2:17]1)([CH3:12])([CH3:11])[CH3:10].C1COCC1.[OH2:27]>[Os](=O)(=O)(=O)=O>[OH:27][CH:19]([C:16]1([NH:15][C:14](=[O:21])[O:13][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:17][CH2:18]1)[CH2:20][OH:5]

Participants

5

Reactant 3

HCID 82029Methyl morpholine oxideHCID 21881883Oxolane--water (1/1)HCID 68996832HCID 68996832, compound

Product 1

HCID 131734578HCID 131734578, compound

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

A catalytic amount of osmium tetroxide (<1 mg) and 4-methylmorpholine N-oxide (70 mg, 0.6 mmol) were added to a solution of tert-butyl(1-ethenylcyclopropyl)carbamate (0.10 g, 0.55 mmol) in THF/water (5 mL/5 mL). The mixture was stirred at room temperature overnight and then concentrated under reduced pressure. The residue was purified by chromatography on silica gel (methanol/dichloromethane) to give tert-butyl [1-(1,2-dihydroxyethyl)cyclopropyl]carbamate. 1H NMR (400 MHz, CD3OD): δ 3.63-3.60 (m, 1H), 3.52-3.48 (m, 1H), 3.21-3.18 (m, 1H), 1.43 (s, 9H), 0.91-0.89 (m, 1H), 0.80-0.75 (m, 2H), 0.68-0.67 (m, 1H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by chromatography on silica gel (methanol/dichloromethane)

Sources & evidence

ORD record
ord-ea60a801e58b4c79a866426a18f8d1df
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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