(2S,4S)-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid → (2S,4R)-tert-butyl 2-(N-(oct-6-enyl)-N-methylcarbamoyl)-4-hydroxypyrrolidine-1-carboxylate

HRID 420054Notes

Reaction equation

HRID 420054 reaction equation
S([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)(O)(=O)=O.CNCCCCC=CCC.C(N1C[C@@H](O)C[C@H]1C(O)=O)(OC(C)(C)C)=O.[CH2:38]([N:44]([CH3:60])[C:45]([C@@H:47]1[CH2:51][C@@H:50]([OH:52])[CH2:49][N:48]1[C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])=[O:46])CCCC=C>>[CH2:38]([N:44]([CH3:60])[C:45]([C@@H:47]1[CH2:51][C@@H:50]([OH:52])[CH2:49][N:48]1[C:53]([O:55][C:56]([CH3:58])([CH3:57])[CH3:59])=[O:54])=[O:46])[CH2:7][CH2:6][CH2:5][CH2:11][CH:10]=[CH:8][CH3:9]

Participants

4

Reactant 3

HCID 688614(2S,4S)-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acidHCID 57816706(2S,4R)-tert-butyl 2-(N-(hex-5-enyl)-N-methyl-carbamoyl)-4-hydroxypyrrolidine-1-carboxylateHCID 131729113n-Methyloct-5-en-1-amine tosylate salt

Product 1

HCID 66650516(2S,4R)-tert-butyl 2-(N-(oct-6-enyl)-N-methylcarbamoyl)-4-hydroxypyrrolidine-1-carboxylate

Procedure

Compound 70b was synthesized from compound 32c and cis-N-Boc-4-hydroxy-L-proline as yellow oil in quantitative yield, following the procedure as described for compound 48.

Sources & evidence

ORD record
ord-0ac373ad74304b6aaae19c4b88be2ccb
Source dataset
uspto-grants-2012_01
Patent number
US08093379B2

Reaction notes

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