Triethylamine → 6-methoxy-3,4,4a,5,10,10a-hexahydro-2H-naphtho-[2,3-b][1,4]oxazine-4-carboxylic acid benzyl ester

HRID 975931Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:4]=1[CH2:5][CH:6]1[NH:11][CH2:10][CH2:9][O:8][CH:7]1[CH2:12]2.C(N(CC)CC)C.Cl[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26].CCOC(C)=O.C(Cl)Cl>C(Cl)Cl.CCOC(C)=O>[CH2:28]([O:27][C:25]([N:11]1[CH2:10][CH2:9][O:8][CH:7]2[CH2:12][C:13]3[C:4]([CH2:5][CH:6]12)=[C:3]([O:2][CH3:1])[CH:16]=[CH:15][CH:14]=3)=[O:26])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 6-methoxy-3,4,4a,5,10,10 a-hexahydro-2H-naphtho-[2,3-b][1,4]oxazine (0.62 g, 2.7 mmol) in 10 ml of CH2Cl2 was added triethylamine (1.0 ml, 7.2 mmol ) and benzyl chloroformate (0.6 ml, 4.1 mmol). The resulting mixture was stirred at 25° C. for 3 h. It was then diluted with 100 ml of EtOAc and washed with brine. The organic layer was dried over Na2SO4 and concentrated in vacuo, yielding an oily residue which was subjected to column chromatography (20% EtOAc-CH2Cl2) to provide 0.46 g (48%) of the desired product. 1H NMR (300 MHz, CDCl3): δ 2.45 (dd, 1H, J=10.6, 16.6 Hz), 2.83 (dd, 1H, J=10.3, 16.0 Hz), 3.04 (dd, 1H, J=5.0, 16.0 Hz), 3.68-3.88 (m, 6H), 3.76 (s, 3H), 4.02(m, 1H), 5.16 (AB q, 2H, J=17.6 Hz), 6.66 (m, 2H), 7.09 (t, 1H,J=7.8 Hz).

Workup

washwashed with brine
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated in vacuo
customyielding an oily residue which

Sources & evidence

ORD record: ord-0fcb3949101049ba9713143bba6ed958
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05610174

Reaction notes

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