(R)-(-)-2-Amino-1-propanol → HCID 11661718, compound

HRID 1247590Notes

Reaction equation

HRID 1247590 reaction equation
[C:1]12([CH2:11][NH:12][C:13](=[O:25])[C:14]3[CH:19]=[C:18]([CH2:20][CH2:21][CH:22]=O)[CH:17]=[N:16][C:15]=3[Cl:24])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[NH2:26][C@H:27]([CH3:30])[CH2:28][OH:29].C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[C:1]12([CH2:11][NH:12][C:13](=[O:25])[C:14]3[CH:19]=[C:18]([CH2:20][CH2:21][CH2:22][NH:26][C@H:27]([CH3:30])[CH2:28][OH:29])[CH:17]=[N:16][C:15]=3[Cl:24])[CH2:2][CH:3]3[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]3)[CH2:8]1)[CH2:10]2

Participants

6

Reactant 3

HCID 80308(R)-(-)-2-Amino-1-propanolHCID 5003444Sodium cyanoborohydrideHCID 21906677HCID 21906677, compound

Product 1

HCID 11661718HCID 11661718, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

The titled compound was prepared from N-(1-adamantylmethyl)-2-chloro-5-(3-oxopropyl)nicotinamide (Example 3(ii)) (0.10 g), (R)-2-aminopropanol (0.046 g) and sodium cyanoborohydride (0.020 g) in methanol (3 ml) and acetic acid (0.1 ml) by the method of Example 3(iii). The product was purified by chromatography on silica gel eluting with 0.7M anhydrous ammonia in methanol:ethyl acetate (1:5) to afford the titled compound as an oil (0.085 g).

Workup

  1. customThe product was purified by chromatography on silica gel eluting with 0.7M anhydrous ammonia in methanol:ethyl acetate (1:5)

Sources & evidence

ORD record
ord-b60e2aa12e3f4e1c8e9df7bf00fe463c
Source dataset
uspto-grants-2006_10
Patent number
US07129246B2

Reaction notes

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