2-Amino-2-methyl-1-propanol → HCID 46837786, compound

HRID 1399536Notes

Reaction equation

HRID 1399536 reaction equation
O[C@H:2]([CH3:15])[C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1)=[O:4].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.[NH2:47][C:48]([CH3:52])([CH3:51])[CH2:49][OH:50]>CC#N>[C:5]1([C@:3]2([OH:4])[O:50][CH2:49][C:48]([CH3:52])([CH3:51])[NH:47][C@H:2]2[CH3:15])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 118072-Amino-2-methyl-1-propanolHCID 67749Trifluoromethanesulfonic anhydrideHCID 88675Proton spongeHCID 46838209HCID 46838209, compound

Product 1

HCID 46837786HCID 46837786, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 4q was synthesized by a procedure similar to that described for (2S,3S)-4a employing (R)-2-hydroxy-1-(naphthalen-1-yl)propan-1-one (10h, 1.15 g, 0.058 mol), Proton sponge (1.5 g, 0.070 mol), triflic anhydride (1.1 mL, 64 mmol), and 2-amino-2-methyl-1-propanol (1.1 g, 0.012 mol) in CH3CN (45 mL). After purification, 1.35 g (86%) of the free base 4q was isolated and converted to the D-tartrate salt, which was recrystallized from H2O-MeOH-Et2O solvent system: mp 115-116+C.; [α]20D −9.5° (c 0.74, CH3OH); 1H NMR (methanol-d4) δ 8.89 (d, 1H, J=8.4 Hz), 7.97-7.89 (m, 3H), 7.54-7.50 (m, 3H), 4.33 (s, 1H), 3.70 (d, 1H, J=12.2 Hz), 3.48 (q, 1H, J=7.0 Hx), 1.77 (s, 3H), 1.41 (s, 3H), 0.96 (d, 3H, J=6.6 Hz); 13C NMR (methanol-d4) δ 136.5, 132.3, 131.9, 130.5, 130.2, 128.1, 127.4, 127.0, 126.1, 99.0, 75.1, 68.1, 67.3, 53.9, 24.8, 22.9, 15.8, 15.2; LCMS (ESI) m/z 272.3 [(M-tartrate)+, M=C19H24NO5]; Anal. (C19H24NO5.0.75H2O) calcd: C, 63.41; H, 7.14; N, 3.89. found: C, 63.63; H, 7.44; N, 3.70.

Workup

  1. customCompound 4q was synthesized by a procedure similar to
  2. customAfter purification

Sources & evidence

ORD record
ord-4694a27eb316451c867d0c4d9d32594f
Source dataset
uspto-grants-2014_12
Patent number
US08906908B2

Reaction notes

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