Lithium tri-s-butylborohydride → trans-2,2,2-trifluoro-N-(3-hydroxy-4,6-dimethyl-2,3-dihydro-1H-inden-1-yl)acetamide

HRID 501755Notes

Reaction equation

HRID 501755 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([NH:5][C@H:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH3:15])[CH:13]=2)[C@@H:8]([OH:16])[CH2:7]1)=[O:4].[CH2:19](O[C@H]1C2C(=CC(OCCC)=CC=2)[C@@H](N)C1)C=C.CCC(C)[BH-](C(C)CC)C(C)CC.[Li+]>>[F:1][C:2]([F:17])([F:18])[C:3]([NH:5][C@H:6]1[C:14]2[C:9](=[C:10]([CH3:19])[CH:11]=[C:12]([CH3:15])[CH:13]=2)[C@H:8]([OH:16])[CH2:7]1)=[O:4]

Participants

4

Reactant 3

HCID 3611392Lithium tri-s-butylborohydrideHCID 59423826(1S,3R)-3-(Allyloxy)-6-propoxy-2,3-dihydro-1H-inden-1-amine2×HCID 59423834HCID 59423834, compound

Product 1

HCID 86622366trans-2,2,2-trifluoro-N-(3-hydroxy-4,6-dimethyl-2,3-dihydro-1H-inden-1-yl)acetamideYield 85%

Procedure

Step BM (2): The crude product from Step BM (1) was reduced with L-selectride by following a procedure analogous to Step BJ (1) to afford 6.5 g (85% yield) of trans-2,2,2-trifluoro-N-(3-hydroxy-4,6-dimethyl-2,3-dihydro-1H-inden-1-yl)acetamide (6.5 g, 85% yield). LC-MS (M+H)+=274.10 1H NMR (500 MHz, CDCl3) δ ppm 7.32 (d, 1H) 6.98-7.03 (m, 1H) 6.93-6.97 (m, 1H) 5.22 (t, 1H) 5.12 (d, 1H) 2.81-2.98 (m, 1H) 2.64-2.74 (m, 1H) 2.32-2.37 (m, 3H) 2.27-2.32 (m, 3H) 1.94 (d, 1H).

Sources & evidence

ORD record
ord-830ea194ea564d61ba07d72d5d3ec3cb
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

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