Triphenylphosphine → (S)-2-(1-Benzyl-1H-tetrazol-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester

HRID 1185563Notes

Reaction equation

HRID 1185563 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16](=O)[NH:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.C[Si]([N:63]=[N+:64]=[N-:65])(C)C.N([O-])=O.[Na+]>C(#N)C.O>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16]1[N:17]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:65]=[N:64][N:63]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 11776TriphenylphosphineHCID 78378AzidotrimethylsilaneHCID 690250(S)-2-Benzylcarbamoyl-pyrrolidine-1-carboxylic acid benzyl esterHCID 5363146Diisopropyl azodicarboxylateHCID 23668193Sodium Nitrite

Product 1

HCID 66857129(S)-2-(1-Benzyl-1H-tetrazol-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a suspension of 1.50 g (S)-2-Benzylcarbamoyl-pyrrolidine-1-carboxylic acid benzyl ester and 2.91 g triphenylphosphine in 30 ml acetonitrile were added dropwise at 0° C. 2.3 ml diisopropylazodicarboxylate and after 2 minutes 1.5 ml trimethylsilylazide over a period of 20 minutes. After 30 minutes the mixture was allowed to warm to RT and stirred for 12 h. The mixture was cooled to 0° C. and 1.5 ml aqueous sodium nitrite (2.9 M) were added, after 30 minutes a solution of 2.4 g ceric ammonium nitrate in 15 ml water was added and stirred for another 20 minutes. After this time the mixture was poured into ice and extracted twice with dichloromethane.

Workup

  1. additionwere added dropwise at 0° C
  2. temperatureThe mixture was cooled to 0° C.
  3. additionwas added
  4. stirringstirred for another 20 minutes
  5. additionAfter this time the mixture was poured into ice
  6. extractionextracted twice with dichloromethane

Sources & evidence

ORD record
ord-fc912d52974842fc912a1b50ac818e8d
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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