1,1-Dimethylethyl 1-thia-6-azaspiro[2.5]octane-6-carboxylate → tert-Butyl 4-mercapto-4-methylpiperidine-1-carboxylate

HRID 524911Notes

Reaction equation

HRID 524911 reaction equation
[S:1]1[C:3]2([CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]2)[CH2:2]1.NC1C(C(ON2C3C=CC=CC=3N=N2)=O)=C2N=CC(CC#N)=CN2N=1>C1COCC1>[CH3:2][C:3]1([SH:1])[CH2:4][CH2:5][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 181879711,1-Dimethylethyl 1-thia-6-azaspiro[2.5]octane-6-carboxylateHCID 901998921H-benzo[d][1,2,3]triazol-1-yl 2-amino-6-(cyanomethyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate

Product 1

HCID 71629631tert-Butyl 4-mercapto-4-methylpiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 1-thia-6-azaspiro[2.5]octane-6-carboxylate (430 mg, 1.875 mmol) in THF (5 mL) was added LiAlH4 (Lithium Ion (1)) (0.9375 mL of 2 M, 1.875 mmol) and the solution was stirred at room temperature for 1 h. The reaction was quenched by careful dropwise addition of water (2 ml), stirred for 10 mins before the reaction mixture was partitioned between water and EtOAc. The organic extract was washed with brine, dried (MgSO4) and concentrated to give tert-butyl 4-methyl-4-sulfanyl-piperidine-1-carboxylate as a colorless oil. (380 mg, 87%). MS (ES−) 231.0.

Workup

  1. customThe reaction was quenched by careful dropwise addition of water (2 ml)
  2. stirringstirred for 10 mins before the reaction mixture
  3. customwas partitioned between water and EtOAc
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-65edc1348a874e629453bfd658f3a1ee
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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