(R)-3-Pyrrolidinol → (R)-tert-Butyl 4-(3-hydroxypyrrolidin-1-yl)benzoate

HRID 1805287Notes

Reaction equation

HRID 1805287 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:19]=[CH:18][C:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:9][CH:8]=2)[CH2:3]1.O[C@@H]1CCNC1>>[OH:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:19]=[CH:18][C:10]([C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])=[CH:9][CH:8]=2)[CH2:3]1

Participants

3

Reactant 2

HCID 2759337(R)-3-PyrrolidinolHCID 58417032HCID 58417032, compound

Product 1

HCID 58930590(R)-tert-Butyl 4-(3-hydroxypyrrolidin-1-yl)benzoateYield 91%

Procedure

Title compound II was obtained in 91% yield by following the procedure described above for the synthesis of compound 157 (scheme 5, step 1) but substituting (S)-hydroxypyrrolidine for (R)-3-hydroxypyrrolidine. 1H NMR (DMSO-d6) δ(ppm): 7.69 (d, J=8.8 Hz, 2H), 6.51 (d, J=8.8 Hz, 2H), 5.02 (d, J=2.4 Hz, 1H), 4.40 (bs, 1H), 3.43 (dd, J=10.6, 4.6 Hz, 1H), 3.37 (m, 1H), 3.32 (m, 1H), 3.14 (d, J=10.8, 1H), 2.03 (m, 1H), 1.91 (m, 1H), 1.50 (s, 9H). LRMS (ESI): (calc) 263.15 (found) 264.1 (MH).

Sources & evidence

ORD record
ord-4b9f07e1ba564b3681537ddfdf546329
Source dataset
uspto-grants-2013_01
Patent number
US08354445B2

Reaction notes

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