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Potassium Carbonate → tert-butyl (3S)-3-ethynylpiperidine-1-carboxylate

HRID 1465682
Notes
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Reaction equation

HRID 1465682 reaction equation
[CH:1]([C@@H:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1)=O.[N+](=[C:18](P(=O)(OC)OC)C(=O)C)=[N-].C([O-])([O-])=O.[K+].[K+]>CO>[C:1]([C@@H:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1)#[CH:18]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 42325667tert-Butyl (3R)-3-formylpiperidine-1-carboxylateHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 52420760tert-butyl (3S)-3-ethynylpiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To crude (R)-tert-butyl 3-formylpiperidine-1-carboxylate in MeOH (20 mL) was added dimethyl 1-diazo-2-oxopropylphosphonate (1.28 g, 5.6 mmol), cooled to 0° C. and then added K2CO3 (2.56 g, 18.6 mmol), followed by MS, TLC. Added water (60 mL), extracted with EtOAc (3×50 mL), organic layer were evaporated and dried to give the desired product (S)-tert-butyl 3-ethynylpiperidine-1-carboxylate (0.86 g).

Workup

  1. extractionAdded water (60 mL), extracted with EtOAc (3×50 mL), organic layer
  2. customwere evaporated
  3. customdried

Sources & evidence

ORD record
ord-439e4a2809d0414295308e1c0b251c21
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08999966B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes