N-((1S,3R)-3-(allyloxy)-4,6-Dimethyl-2,3-dihydro-1H-inden-1-yl)-2,2,2-trifluoroacetamide → (1S,3R)-3-(allyloxy)-4,6-dimethyl-2,3-dihydro-1H-inden-1-amine

HRID 501756Notes

Reaction equation

HRID 501756 reaction equation
C(O[C@H]1C2C(=CC(OCCC)=CC=2)[C@@H](N)C1)C=C.[CH2:19]([O:22][C@H:23]1[C:31]2[C:26](=[CH:27][C:28]([CH3:33])=[CH:29][C:30]=2[CH3:32])[C@@H:25]([NH:34]C(=O)C(F)(F)F)[CH2:24]1)[CH:20]=[CH2:21].FC(F)(F)C(N[C@H]1C2C(=CC=C(C)C=2)[C@@H](O)C1)=O>>[CH2:19]([O:22][C@H:23]1[C:31]2[C:26](=[CH:27][C:28]([CH3:33])=[CH:29][C:30]=2[CH3:32])[C@@H:25]([NH2:34])[CH2:24]1)[CH:20]=[CH2:21]

Participants

4

Reactant 3

HCID 59423791N-((1S,3R)-3-(allyloxy)-4,6-Dimethyl-2,3-dihydro-1H-inden-1-yl)-2,2,2-trifluoroacetamideHCID 59423826(1S,3R)-3-(Allyloxy)-6-propoxy-2,3-dihydro-1H-inden-1-amineHCID 59423834HCID 59423834, compound

Product 1

HCID 68464243(1S,3R)-3-(allyloxy)-4,6-dimethyl-2,3-dihydro-1H-inden-1-amineYield 94%

Procedure

Step BN (1): N-((1S,3R)-3-(allyloxy)-4,6-Dimethyl-2,3-dihydro-1H-inden-1-yl)-2,2,2-trifluoroacetamide from Preparation BM was N-deprotected by a procedure analogous to Step U (2) to afford 900 mg (94% yield) of (1S,3R)-3-(allyloxy)-4,6-dimethyl-2,3-dihydro-1H-inden-1-amine as a white solid. LC-MS (M+H)+=218.15; 1H NMR (500 MHz, CDCl3) δ ppm 7.00 (s, 1H) 6.90 (s, 1H) 5.91-6.04 (m, 1H) 5.26-5.34 (m, 1H) 5.13-5.20 (m, J=10.38, 1.53 Hz, 1H) 4.18-4.05 (m, 2H) 4.05-4.00 (m, 1H) 2.57-2.67 (m, 1H) 2.34 (s, 3H) 2.32 (s, 3H) 1.80-1.92 (m, 4H).

Sources & evidence

ORD record
ord-0e4960afea2e45ca9fd674d3421f53ae
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

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