Sodium Hydroxide → HCID 59367312, compound

HRID 1923990Notes

Reaction equation

HRID 1923990 reaction equation
[N:1]([C@H:4]([C:19](=[O:31])[NH:20][C:21]1[CH:22]=[N:23][C:24]2[C:29]([CH:30]=1)=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)=[N+]=[N-].[OH-].[Na+].P(C)(C)C>C1COCC1>[NH2:1][C@H:4]([C:19](=[O:31])[NH:20][C:21]1[CH:22]=[N:23][C:24]2[C:29]([CH:30]=1)=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:17])([CH3:18])[CH3:16])=[O:13])[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 68983TrimethylphosphineHCID 59366992HCID 59366992, compound

Product 1

HCID 59367312HCID 59367312, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-[(2S)-2-azido-2-[(quinolin-3-yl)carbamoyl]ethyl]piperidine-1-carboxylate LXXVIII (262 mg, 0.62 mmol) in THF (20 mL) and 0.1 M NaOH (2.0 mL) was added Me3P (1 M in THF, 0.65 mL). The reaction was stirred at r.t. overnight. The solvent was removed under reduced pressure to give crude tert-butyl 4-[(2S)-2-amino-2-[(quinolin-3-yl)carbamoyl]ethyl]piperidine-1-carboxylate LXXIX (275 mg), which was directly used in step 8. ESIMS found for C22H30N4O3 m/z 399 (M+H).

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ef550344861e4ee4a933b0ff622b7e89
Source dataset
uspto-grants-2012_05
Patent number
US08178490B2

Reaction notes

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