Trifluoroacetic acid → (3r,4r)-Rel-4-azido-3-methoxypiperidine

HRID 723466Notes

Reaction equation

HRID 723466 reaction equation
[N:1]([C@@H:4]1[CH2:9][CH2:8][N:7](C(OC(C)(C)C)=O)[CH2:6][C@H:5]1[O:17][CH3:18])=[N+:2]=[N-:3].C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:1]([C@@H:4]1[CH2:9][CH2:8][NH:7][CH2:6][C@H:5]1[O:17][CH3:18])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58745528(3r,4r)-Rel-tert-butyl 4-azido-3-methoxypiperidine-1-carboxylate

Product 1

HCID 91094414(3r,4r)-Rel-4-azido-3-methoxypiperidineYield 206.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 247A (310 mg, 1.21 mmol) in 2 mL of CH2Cl2 at room temperature was added TFA (2.00 mL, 26.0 mmoL). This mixture was stirred at room temperature for 15 min and concentrated in vacuo to give 390 mg of (3R,4R)-rel-4-azido-3-methoxypiperidine as the TFA salt. Compound 247B was prepared from this TFA salt (52.0 mg, 0.19 mmoL) in a similar process as described for 146E. It had an analytical HPLC retention time=1.97 min. (Phenomenox S5 C18-HC 4.6×50 mm column, 10–90% aqueous methanol over 4 minutes containing 0.1% TFA, 4 ml/min, monitoring at 220 nm) and a LC/MS M++1=409.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6af6a19f162b4a5c8e85f7bea657e75c
Source dataset
uspto-grants-2006_11
Patent number
US07141571B2

Reaction notes

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