2-Amino-2-methyl-1-propanol → HCID 46837647, compound

HRID 1399524Notes

Reaction equation

HRID 1399524 reaction equation
[C:1]1([C:7](=[O:11])[C@H:8](O)[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C1C2C(N(C)C)=CC=CC=2C=CC=1)C.S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O.[NH2:43][C:44]([CH3:48])([CH3:47])[CH2:45][OH:46]>C(Cl)Cl>[C:1]1([C@:7]2([OH:11])[O:46][CH2:45][C:44]([CH3:48])([CH3:47])[NH:43][C@H:8]2[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 118072-Amino-2-methyl-1-propanolHCID 67749Trifluoromethanesulfonic anhydrideHCID 88675Proton spongeHCID 118049351-Propanone, 2-hydroxy-1-phenyl-, (2R)-

Product 1

HCID 46837647HCID 46837647, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 4b was synthesized by a procedure similar to that described for (2S,3S)-4a using (R)-1-phenyl-2-hydroxypropan-1-one (10b, 3.49 g, 0.0233 mol), Proton sponge (5.9 g), triflic anhydride (4.2 mL, 26 mmol), and 2-amino-2-methyl-1-propanol (4.6 g, 0.052 mol) in CH2Cl2 (50 mL). After purification by chromatography on silica gel, 3.52 g (68%) of the free base 4b was isolated, and converted to 1.19 g of the hemi-D-tartrate salt, which had >99% ee: mp 112-113° C.; [α]20D +15.8° (c 1.1, CH3OH); 1H NMR (methanol-d4) δ 7.61-7.59 (m, 2H), 7.44-7.36 (m, 3H), 4.32 (s, 1H), 4.24 (d, 1H, J=12.3 Hz), 3.58-3.48 (m, 2H), 1.64 (s, 3H), 1.39 (s, 3H), 1.09 (d, 3H, J=6.6 Hz); 13C NMR (methanol-d4) δ 179.1, 142.4, 130.3, 129.6 (2C), 127.9 (2C), 97.3, 75.4, 67.4, 55.47, 55.27, 24.1, 21.3, 14.3; LCMS (ESI) m/z 222.4 (M-tartrate)+; Anal. (C15H22NO5.0.5H2O) calcd: C, 59.00; H, 7.59; N, 4.59. found: C, 58.77; H, 7.46; N, 4.64.

Workup

  1. customCompound 4b was synthesized by a procedure similar to
  2. customAfter purification by chromatography on silica gel

Sources & evidence

ORD record
ord-295f6dd3830b4628949389d81b8a3c3e
Source dataset
uspto-grants-2014_12
Patent number
US08906908B2

Reaction notes

Loading…