Acetic Acid → HCID 117698124, compound

HRID 1778492Notes

Reaction equation

HRID 1778492 reaction equation
C(C[C@@H:4]1[CH2:10][CH:9]2[N:11](C(OC(C)(C)C)=O)[CH:5]1[CH2:6][O:7][CH2:8]2)#N.[C:19]([OH:22])(=[O:21])[CH3:20]>Cl>[CH:9]12[NH:11][CH:5]([C@H:4]([CH2:20][C:19]([OH:22])=[O:21])[CH2:10]1)[CH2:6][O:7][CH2:8]2

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 131734813HCID 131734813, compound

Product 1

HCID 117698124HCID 117698124, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of tert-butyl (6S)-6-(cyanomethyl)-3-oxa-8-azabicyclo[3.2.1]octane-8-carboxylate 64b (180 mg, 0.71 mmol) in Conc. HCl (5 mL) and acetic acid (1 mL) was stirred at 100° C. for 4 h. Then the mixture concentrated in vacuo to afford 2-[(6S)-3-oxa-8-azabicyclo[3.2.1]octan-6-yl]acetic acid 64c (121 mg, 99%) which was used for next step without further purification. MS: calc'd (MH+) 172, measured (MH+) 172.

Workup

  1. concentrationThen the mixture concentrated in vacuo

Sources & evidence

ORD record
ord-ea7bc728490746739cd1be36303dc3aa
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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