4-(N-(4-nitrobenzyloxycarbonyl)(N-allyl)amino)piperidine hydrochloride → 1-(R)-(N-(methyl)-N-(t-butoxycarbonyl)amino)-3-(S)-((4-(N-(4-nitrobenzyloxycarbonyl)-N-(allyl)amino)piperidin-1-yl)methyl)-4-(S)-phenylcyclopentane

HRID 2301769Notes

Reaction equation

HRID 2301769 reaction equation
[CH3:1][N:2]([C@@H:10]1[CH2:14][C@H:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C@@H:12]([CH2:21]O)[CH2:11]1)[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].Cl.[N+:24]([C:27]1[CH:46]=[CH:45][C:30]([CH2:31][O:32][C:33]([N:35]([CH:39]2[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)[CH2:36][CH:37]=[CH2:38])=[O:34])=[CH:29][CH:28]=1)([O-:26])=[O:25]>>[CH3:1][N:2]([C@@H:10]1[CH2:14][C@H:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C@@H:12]([CH2:21][N:42]2[CH2:43][CH2:44][CH:39]([N:35]([C:33]([O:32][CH2:31][C:30]3[CH:29]=[CH:28][C:27]([N+:24]([O-:26])=[O:25])=[CH:46][CH:45]=3)=[O:34])[CH2:36][CH:37]=[CH2:38])[CH2:40][CH2:41]2)[CH2:11]1)[C:3]([O:5][C:6]([CH3:9])([CH3:7])[CH3:8])=[O:4]

Participants

3

Reactant 2

HCID 181876754-(N-(4-nitrobenzyloxycarbonyl)(N-allyl)amino)piperidine hydrochlorideHCID 183450901-(r)-(n-(Methyl)-n-(t-butoxycarbonyl)amino)-3-(s)-(hydroxymethyl)-4-(s)-phenylcyclopentane

Product 1

HCID 183450891-(R)-(N-(methyl)-N-(t-butoxycarbonyl)amino)-3-(S)-((4-(N-(4-nitrobenzyloxycarbonyl)-N-(allyl)amino)piperidin-1-yl)methyl)-4-(S)-phenylcyclopentane

Procedure

Using essentially the same procedures as in Example 11, Steps C and D but starting with 1-(R)-(N-(methyl)-N-(t-butoxycarbonyl)amino)-3-(S)-(hydroxymethyl)-4-(S)-phenylcyclopentane (Higher Rf isomer) from Step G (257 mg, 0.84 mmol) and using 4-(N-(4-nitrobenzyloxycarbonyl)-N-(allyl)amino)piperidine hydrochloride, the title compound was obtained and was the same as the racemic product from Example 15, [α]D=+15.9 (MeOH, c=0.21).

Sources & evidence

ORD record
ord-9f7f946574b840d5a8eaab1af79b4ec7
Source dataset
uspto-grants-2002_12
Patent number
US06500844B1

Reaction notes

Loading…