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

HRID 501752Notes

Reaction equation

HRID 501752 reaction equation
FC(F)(F)C([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.[CH2:19](O[C@H]1C2C(=CC(OCCC)=CC=2)[C@@H](N)C1)[CH:20]=[CH2:21]>>[CH2:21]([O:16][C@H:8]1[C:9]2[C:14](=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[C@@H:6]([NH2:5])[CH2:7]1)[CH:20]=[CH2:19]

Participants

3

Reactant 2

HCID 59423826(1S,3R)-3-(Allyloxy)-6-propoxy-2,3-dihydro-1H-inden-1-amineHCID 59423834HCID 59423834, compound2×

Product 1

HCID 68466237(1S,3R)-3-(allyloxy)-6-methyl-2,3-dihydro-1H-inden-1-amineYield 75%

Procedure

Step BK (2): The product from Step BK (1) was N-deprotected by a procedure analogous to Step U (2) to afford 480 mg (75% yield) of (1S,3R)-3-(allyloxy)-6-methyl-2,3-dihydro-1H-inden-1-amine as a white solid. LC-MS (M+H)+=204.13 1H NMR (500 MHz, CDCl3) δ ppm 7.28 (d, 1H) 7.18 (d, 1H) 7.08 (d, 1H) 6.01-5.94 (m, 1H) 5.32 (d, 1H) 5.18 (d, 1H) 4.77 (t, 1H) 4.16-4.19 (m, 3H) 2.80-2.75 (m, 1H) 2.36 (s, 3H) 1.75-1.70 (m, 3H).

Sources & evidence

ORD record
ord-ae6e535c86f5413e813e70d99f42373c
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

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