Benzyl Alcohol → Benzyl [1-(3-methoxyphenyl)-1-methylethyl]carbamate

HRID 852570Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([CH3:14])([CH3:13])C(O)=O)[CH:6]=[CH:7][CH:8]=1.CC[N:17]([CH2:20]C)CC.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])C=CC=CC=1.[CH2:39]([OH:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C1(C)C=CC=CC=1>[CH2:39]([O:46][C:20](=[O:29])[NH:17][C:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)([CH3:13])[CH3:14])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-(3-methoxy-phenyl)-2-methyl-propionic acid (D99) (1 g, 5.15 mmol, 1 equiv) in toluene (20 ml) at room temperature was added NEt3 (1.07 ml, 7.72 mmol, 1.5 equiv) and then diphenylphosphoryl azide (2.2 ml, 10.3 mmol, 2 equiv). The resulting mixture was then heated at 80° C. for 2 h then benzyl alcohol (1.61 ml, 15.45 mmol, 3 equiv) was added and the solution heated for a further 2 h, cooled to room temperature and partitioned between EtOAc and a saturated NaHCO3 aqueous solution. The two layers were separated and the aqueous phase dried over MgSO4 and concentrated. in vacuo. Purification of the residue by flash chromatography on silica gel (iso-hexane/AcOEt: 9/1) gave [1-(3-methoxy-phenyl)-1-methyl-ethyl]-carbamic acid benzyl ester (D100) (1 g, 65%) a yellow gum.

Workup

temperaturethe solution heated for a further 2 h
temperaturecooled to room temperature
custompartitioned between EtOAc
customThe two layers were separated
dry with materialthe aqueous phase dried over MgSO4
concentrationconcentrated
customPurification of the residue by flash chromatography on silica gel (iso-hexane/AcOEt: 9/1)

Sources & evidence

ORD record: ord-4e52f4e85cd94b1f8b7201628d1121fe
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253198B2

Reaction notes

Loading…