(1R,2R)-2-aminocyclopentan-1-ol hydrochloride → HCID 178523571, compound

HRID 2368797Notes

Reaction equation

HRID 2368797 reaction equation
[F:1][C:2]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:3]=1[CH2:4][C:5]1[CH:6]=[C:7]([C:20](=[O:27])[CH:21]=[C:22]([OH:26])[C:23](O)=[O:24])[C:8](=[O:19])[N:9]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[CH:10]=1.Cl.[NH2:34][C@@H:35]1[CH2:39][CH2:38][CH2:37][C@H:36]1[OH:40]>CO>[F:1][C:2]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:3]=1[CH2:4][C:5]1[CH:6]=[C:7]([C:20](=[O:27])[CH:21]=[C:22]([OH:26])[C:23]([NH:34][C@@H:35]2[CH2:39][CH2:38][CH2:37][C@H:36]2[OH:40])=[O:24])[C:8](=[O:19])[N:9]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[CH:10]=1

Participants

4

Reactant 2

HCID 12886906(1R,2R)-2-aminocyclopentan-1-ol hydrochlorideHCID 178525986HCID 178525986, compound

Product 1

HCID 178523571HCID 178523571, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The titled compound was synthesized using the procedure described above using compound 8. The coupling compound, (1R,2R)-2-aminocyclopentanol hydrochloride, was synthesized by modification of the following procedure: Overman L. E.; Sugai, S., J. Org. Chem. 50, 4154-4155 (1985). The product was a yellow solid, mp 55-57° C., [α20D] −28.5 (c 0.1, MeOH), UV (MeOH) 396 nm (ε 14,100), 319 nm (ε 7444). 1H NMR (CDCl3, 500 MHZ): δ 15.41 (bs, 1H), 8.16 (s, 1H), 8.07 (s, 1H), 7.60-6.84 (m, 9H), 5.21 (s, 2H), 4.10-3.76 (m, 5H), 2.25-1.73 (m, 6H). 13C NMR (CDCl3, 125 MHZ): δ 181.1, 163.0, 162.1, 160.2, 159.0, 143.7, 141.4, 132.1, 132.1, 132.1, 131.2, 131.1, 131.1, 131.0, 130.5, 130.4, 124.7, 124.7, 122.5, 122.4, 122.3, 121.8, 116.9, 115.5, 115.3, 111.7, 111.7, 111.5, 111.5, 104.4, 104.2, 104.0, 98.1, 79.1, 60.2, 47.5, 32.5, 30.5, 30.4, 21.4. HRMS (M+H)+ calculated mass 527.1794 for C28H26F3N2O5. found 527.1804.

Sources & evidence

ORD record
ord-c8882cd6bbfa45be9520626cdb458ed3
Source dataset
uspto-grants-2014_04
Patent number
US08703801B2

Reaction notes

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