Hydrochloric Acid → (2R,3S)-3-Amino-1-azido-4-cyclohexylbutan-2-ol

HRID 253575Notes

Reaction equation

HRID 253575 reaction equation
C(OC([NH:8][C@@H:9]([CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[C@H:10]([OH:15])[CH2:11][N:12]=[N+:13]=[N-:14])=O)(C)(C)C.Cl>O1CCOCC1>[NH2:8][C@@H:9]([CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[C@H:10]([OH:15])[CH2:11][N:12]=[N+:13]=[N-:14]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 14179442(2R,3S)-3-(t-Butoxycarbonylamino)-1-azido-4-cyclohexylbutan-2-ol

Product 1

HCID 57462034(2R,3S)-3-Amino-1-azido-4-cyclohexylbutan-2-ol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

(2R,3S)-3-(t-Butoxycarbonylamino)-1-azido-4-cyclohexylbutan-2-ol (94 mg, (0.30 mmol) was dissolved in dioxane (1 mL) and treated with 4M HCl in dioxane (1 mL). The reaction was allowed to stir for 2 h at rt. The solvent was evaporated and the hydrochloric acid salt of (3R)-3-(1-hydroxy-5-methoxy-1-(2-phenoxyphenyl)pentyl)-N-(piperidin-3-yl)piperidine-1-carboxamide (˜74 mg) was used directly.

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-24dcb98fe81145238c92f0ac4d94b0a5
Source dataset
uspto-grants-2011_01
Patent number
US07872028B2

Reaction notes

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