4-(Pyrrolidin-3-yl)pyridine → 1-Hydroxy-4-adamantyl 3-(pyridin-4-yl)pyrrolidine-1-carboxylate

HRID 1752320Notes

Reaction equation

HRID 1752320 reaction equation
Cl[C:2]([O:4][CH:5]1[CH:12]2[CH2:13][C:8]3([OH:15])[CH2:9][CH:10]([CH2:14][CH:6]1[CH2:7]3)[CH2:11]2)=[O:3].[N:16]1[CH:21]=[CH:20][C:19]([CH:22]2[CH2:26][CH2:25][NH:24][CH2:23]2)=[CH:18][CH:17]=1>>[N:16]1[CH:21]=[CH:20][C:19]([CH:22]2[CH2:26][CH2:25][N:24]([C:2]([O:4][CH:5]3[CH:12]4[CH2:13][C:8]5([OH:15])[CH2:9][CH:10]([CH2:14][CH:6]3[CH2:7]5)[CH2:11]4)=[O:3])[CH2:23]2)=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 49931054-(Pyrrolidin-3-yl)pyridineHCID 581714991-Hydroxy-4-adamantyl chloroformate

Product 1

HCID 498355471-Hydroxy-4-adamantyl 3-(pyridin-4-yl)pyrrolidine-1-carboxylate

Procedure

A procedure analogous to that described in Example 19 Step 1 was followed using 1-hydroxy-4-adamantyl chloroformate solution and 3-(4-pyridyl)pyrrolidine. The title compound was isolated as a mixture of isomers. LC-MS Method 1 tR=0.90 min, m/z=343, 1H NMR (CD3OD) [selected resonances] 4.69 (s, 0.5H), 4.78 (s, 0.5H), 8.03 (d, 2H), 8.78 (d, 2H)

Sources & evidence

ORD record
ord-86618d3939ae41e683a6f401d6992227
Source dataset
uspto-grants-2015_10
Patent number
US09163012B2

Reaction notes

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