3-Hydroxybenzaldehyde → (1S,3R)-3-(Allyloxy)-6-propoxy-2,3-dihydro-1H-inden-1-amine

HRID 501737

Reaction equation

HRID 501737 reaction equation
FC(F)(F)C([NH:5][C@@H:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[C:8](=[O:17])[CH2:7]1)=O.O[C:21]1[CH:22]=C(C=C[CH:28]=1)C=O.F[C:30](F)(F)[C:31](N[C@@H]1C2C(=CC=C(OC(C)C)C=2)[C@H](O)C1)=O>>[CH2:22]([O:17][C@H:8]1[C:9]2[C:14](=[CH:13][C:12]([O:15][CH2:16][CH2:30][CH3:31])=[CH:11][CH:10]=2)[C@@H:6]([NH2:5])[CH2:7]1)[CH:21]=[CH2:28]

Participants

4

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 1472787(S)-2,2,2-trifluoro-N-(6-methoxy-3-oxo-2,3-dihydro-1H-inden-1-yl)acetamide2×HCID 594236882,2,2-trifluoro-N-((1S,3R)-3-hydroxy-6-isopropoxy-2,3-dihydro-1H-inden-1-yl)acetamide

Product 1

HCID 59423826(1S,3R)-3-(Allyloxy)-6-propoxy-2,3-dihydro-1H-inden-1-amine

Procedure

Step AY (1). (1S,3R)-3-(Allyloxy)-6-propoxy-2,3-dihydro-1H-inden-1-amine was prepared from 3-hydroxybenzaldehyde using a series of procedures analogous to Steps AU (1-5), X (1) and U (2). 1H NMR (300 MHz, CDCl3) δ 0.9-1.0 (t, 3H) 1.6-1.8 (m, 2H) 2.6-2.8 (m, 1H) 3.8-3.9 (t, 2H) 4.0-4.2 (m, 3H) 4.7-4.8 (t, 1H) 5.1-5.4 (m, 2H) 5.8-6.0 (m, 1H) 6.7-6.9 (m, 2H) 7.2-7.3 (d, 1H).

Sources & evidence

ORD record
ord-47cecca7295a4be7a5b7cec1a643a5ab
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Linked notes

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