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

HRID 420053Notes

Reaction equation

HRID 420053 reaction equation
S([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)(O)(=O)=O.CNCCCCC=CC.C(N1C[C@@H](O)C[C@H]1C(O)=O)(OC(C)(C)C)=O.[CH2:37]([N:43](C)[C:44]([C@@H:46]1[CH2:50][C@@H:49]([OH:51])[CH2:48][N:47]1[C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])=[O:45])CCCC=C>>[CH2:9]([N:43]([CH3:37])[C:44]([C@@H:46]1[CH2:50][C@@H:49]([OH:51])[CH2:48][N:47]1[C:52]([O:54][C:55]([CH3:57])([CH3:56])[CH3:58])=[O:53])=[O:45])[CH2:8][CH2:10][CH2:11][CH2:5][CH:6]=[CH2:7]

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 131729112n-Methylhept-5-en-1-amine tosylate salt

Product 1

HCID 66650539(2S,4R)-tert-butyl 2-(N-(hept-6-enyl)-N-methylcarbamoyl)-4-hydroxypyrrolidine-1-carboxylate

Procedure

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

Sources & evidence

ORD record
ord-aed1786705d84d4dbb54dfa0b8fd42db
Source dataset
uspto-grants-2012_01
Patent number
US08093379B2

Reaction notes

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