2-(Phenylmethyl)oxirane → (+)-Styrene oxide

HRID 1510215Notes

Reaction equation

HRID 1510215 reaction equation
[CH:1]([O:14][CH2:15]CC1CCNCC=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)C1C=CC=CC=1.O1CC1CC1C=CC=CC=1>C(O)C>[CH2:15]1[O:14][C@@H:1]1[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 948262-(Phenylmethyl)oxiraneHCID 67057593HCID 67057593, compound

Product 1

HCID 114705(+)-Styrene oxide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

To a stirring solution of cis-(−)-8-benzydryl-1,4-diazabicyclo[3.3.1]nonane 5 (0.100 g, 0.341 mmol) in dry ethanol was added 2,3-epoxypropyl benzene (0.068 g, 0.512 mmol). The reaction mixture was stirred overnight at 65° C. (Procedure A). The diastereomers were separated by preparative TLC using acetone/diethyl ether (20:80) as mobile phase to afford 6a and 6b. Upper Fraction gave 6a (0.026 g, 18%). 1H NMR (400 MHz, CDCl3): δ 1.24-1.43 (2H, m, H-7), 1.54-1.66 (1H, m, H-6a), 2.03-2.06 (1H, m, H6eq), 2.28 (1H, t, J=12.4 Hz, NCH2CH), 2.39 (1H, bs, H-5), 2.57-2.87 (6H, m, NCH2CH, NCH2CH2N, Ph-CH2), 2.98-3.01 (1H, m, H-9ax), 3.10 (1H, bd, J=11.8 Hz, NCH2CH2N), 3.22-3.25 (1H, m, H-9eq) 3.77 (1H, dt, J=4.8 Hz, J=11.2 Hz, H-8ax), 3.84-3.91 (2H, m, CH—OH, (Ph)2CH), 7.11-7.15 (2H, m, ArH), 7.19-7.31 (1H, m, ArH), 7.35-7.38 (2H, m, ArH). [α]25D (oxalate salt)=(−) 24.7° (c 0.42, MeOH).

Workup

  1. customThe diastereomers were separated by preparative TLC

Sources & evidence

ORD record
ord-d1038f2ae7334dd99e5cbf6be13cc7a1
Source dataset
uspto-grants-2012_07
Patent number
US08211916B2

Reaction notes

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