Cyclopentane-1,3-diol → tert-Butyl 4-[({4-[(trans-3-hydroxycyclopentyl)oxy]-1,2-benzisoxazol-3-yl}oxy)methyl]piperidine-1-carboxylate

HRID 2410371Notes

Reaction equation

HRID 2410371 reaction equation
[OH:1][C:2]1[C:7]2[C:8]([O:11][CH2:12][CH:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]3)=[N:9][O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH:26]1(O)[CH2:30][CH2:29][CH:28]([OH:31])[CH2:27]1.OCCC1CCN(C(OC(C)(C)C)=O)CC1>>[OH:31][C@H:28]1[CH2:29][CH2:30][C@H:26]([O:1][C:2]2[C:7]3[C:8]([O:11][CH2:12][CH:13]4[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]4)=[N:9][O:10][C:6]=3[CH:5]=[CH:4][CH:3]=2)[CH2:27]1

Participants

4

Reactant 3

HCID 100165Cyclopentane-1,3-diolHCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidineHCID 136263840HCID 136263840, compound

Product 1

HCID 69319191tert-Butyl 4-[({4-[(trans-3-hydroxycyclopentyl)oxy]-1,2-benzisoxazol-3-yl}oxy)methyl]piperidine-1-carboxylate

Procedure

The title compound was prepared according to the procedure described in Step 2 of EXAMPLE 7 using tert-butyl 4-{[(4-hydroxy-1,2-benzisoxazol-3-yl)oxy]methyl}piperidine-1-carboxylate (EXAMPLE 17, step 2) and 1,3-cyclopentanediol (mixture of isomers, cis:trans=ca. 5:1) instead of 4-(benzyloxy)-1,2-benzisoxazol-3-ol and tert-butyl 4-(2-hydroxyethyl)piperidine-1-carboxylate.

Sources & evidence

ORD record
ord-93640cba850f4f83aeb956d261035a8e
Source dataset
uspto-grants-2014_08
Patent number
US08816090B2

Reaction notes

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