2-Amino-2-methyl-1-propanol → HCID 46837921, compound

HRID 1399537Notes

Reaction equation

HRID 1399537 reaction equation
O[C@H:2]([CH3:15])[C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[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]>C(#N)C>[CH:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:13]=[CH:14][C:5]=1[C@:3]1([OH:4])[O:50][CH2:49][C:48]([CH3:52])([CH3:51])[NH:47][C@H:2]1[CH3:15]

Participants

6

Reactant 4

HCID 118072-Amino-2-methyl-1-propanolHCID 67749Trifluoromethanesulfonic anhydrideHCID 88675Proton spongeHCID 46838210HCID 46838210, compound

Product 1

HCID 46837921HCID 46837921, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 4r was synthesized by a procedure similar to that described for (2S,3S)-4a using (R)-2-hydroxy-1-(naphthalen-2-yl)propan-1-one (10i, 2.5 g, 0.013 mol), Proton sponge (3.24 g, 0.0151 mol), triflic anhydride (2.4 mL, 137 mmol), and 2-amino-2-methyl-1-propanol (2.4 g, 0.027 mol) in acetonitrile (40 mL). After purification, 2.2 g (65%) of the free base 4r was isolated and converted to the hemi-D-tartrate salt: mp 179-180° C.; [α]20D −1.5° (c 0.55, CH3OH); 1H NMR (methanol-d4) δ 8.13-8.12 (m, 1H), 7.95-7.88 (m, 3H), 7.75-7.71 (m, 1H), 7.57-7.50 (m, 2H), 4.33 (s, 1H), 4.25 (d, 1H, J=11.9 Hz), 3.66-3.57 (m, 2H), 1.65 (s, 3H), 1.37 (s, 3H), 1.09 (d, 3H, J=6.6 Hz); 13C NMR (methanol-d4) δ 178.7, 139.9, 135.3, 134.6, 129.8, 129.33, 129.00, 128.0, 127.8, 127.4, 125.4, 97.4, 75.2, 67.7, 55.1, 24.5, 21.6, 14.6; LCMS (ESI) m/z 272.5 [(M-tartrate)+, M=C19H24NO5]; Anal. (C19H24NO5.0.5H2O) calcd: C, 65.88; H, 6.98; N, 4.04. found: C, 65.75; H, 7.03; N, 4.06.

Workup

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

Sources & evidence

ORD record
ord-37a863d8eb12420f98cdaa14fb5da0db
Source dataset
uspto-grants-2014_12
Patent number
US08906908B2

Reaction notes

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