Triethylamine → HCID 86702799, compound

HRID 1425917Notes

Reaction equation

[OH:1][CH2:2][CH:3]1[CH:8]([CH2:9][OH:10])[C@H:7]2[N:11]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])[C@@H:4]1[CH2:5][CH2:6]2.CCN(CC)CC.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>C(Cl)Cl>[CH3:29][S:30]([O:10][CH2:9][CH:8]1[CH:3]([CH2:2][O:1][S:30]([CH3:29])(=[O:32])=[O:31])[C@H:4]2[N:11]([C:12]([O:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[O:13])[C@@H:7]1[CH2:6][CH2:5]2)(=[O:32])=[O:31]

Participants

Conditions

Temperature: -10 °C

Procedure

To a solution of (1R,4S)-benzyl 2,3-bis(hydroxymethyl)-7-azabicyclo[2.2.1]heptane-7-carboxylate (LI) (1.85 g, 6.35 mmol) and Et3N (2.65 mL, 19.05 mmol) in DCM (70 mL) at −30° C. was added a solution of MsCl (1.47 mL, 19.05 mmol) in DCM (15 mL) dropwise. The reaction mixture was stirred for 15 min at −10° C. then for 1.5 h at 0° C. The reaction mixture was dilluted with DCM, washed with 1 M HCl, 1 M K2CO3, brine and then dried over MgSO4. The solvent was removed under vacuum to give (1R,4S)-benzyl 2,3-bis((methylsulfonyloxy)methyl)-7-azabicyclo[2.2.1]heptane-7-carboxylate (LII) as a very thick, light yellow oil (2.70 g, 6.03 mmol, 95% yield). 1H NMR (CDCl3) δ ppm 1.74 (brs, 4H), 1.88 (brs, 1H), 2.16 (brs, 1H), 2.97 (brs, 2H), 3.03 (brs, 3H), 3.97-4.09 (m, 1H), 4.10-4.18 (m, 1H), 4.22 (brs, 1H), 4.26-4.34 (m, 1H), 4.40 (brs, 1H), 5.11 (brs, 2H), 7.35 (brs, 5H); ESIMS found for C18H25NO8S2 m/z 448 (M+H).

Workup

waitfor 1.5 h at 0° C
washwashed with 1 M HCl, 1 M K2CO3, brine
dry with materialdried over MgSO4
customThe solvent was removed under vacuum

Sources & evidence

ORD record: ord-a366d9fbb8ce49a88d366deb7ea4cf8d
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933018B2

Reaction notes

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