Triphenylphosphine → tert-butyl 4-[1-(2-methoxy-2-oxoethyl)-1H-tetraazol-5-yl]piperidine-1-carboxylate

HRID 643575Notes

Reaction equation

HRID 643575 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[C:32]([O:36][CH3:37])(=[O:35])[CH2:33]O.[NH:38]1[C:42]([CH:43]2[CH2:48][CH2:47][N:46]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[CH2:45][CH2:44]2)=[N:41][N:40]=[N:39]1>ClCCl>[CH3:37][O:36][C:32](=[O:35])[CH2:33][N:41]1[C:42]([CH:43]2[CH2:48][CH2:47][N:46]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[CH2:45][CH2:44]2)=[N:38][N:39]=[N:40]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 66774Methyl GlycolateHCID 5462977Diethyl azodicarboxylateHCID 18187701Tert-butyl 4-(2H-tetrazol-5-YL)piperidine-1-carboxylate

Product 1

HCID 68536803tert-butyl 4-[1-(2-methoxy-2-oxoethyl)-1H-tetraazol-5-yl]piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triphenylphosphine (1.28 g, 4.89 mmol), DEAD (804 μL, 4.89 mmol), and methyl glycolate (378 μL, 4.89 mmol) were added to a solution of tert-butyl 4-(1H-tetraazol-5-yl)piperidine-1-carboxylate (619.7 mg, 2.447 mmol) in dichloromethane (20 mL). The reaction mixture was stirred for 16 h at rt and then concentrated under reduced pressure. Purification by MPLC (silica gel, 10-50% EtOAc/hexanes) afforded tert-butyl 4-[1-(2-methoxy-2-oxoethyl)-1H-tetraazol-5-yl]piperidine-1-carboxylate. ESI-MS calculated for C14H23N5O4: 325.36, found 348 (M+Na).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customPurification by MPLC (silica gel, 10-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-8e5d0eb0f0c943378f5a57da26d6fae8
Source dataset
uspto-grants-2010_04
Patent number
US07700591B2

Reaction notes

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